In the 1940's, three men came to define the "Beat Generation:" Jack Kerouac (Johnny Depp), Allen Ginsburg (John Turturro), and William S. Burroughs (Dennis Hopper). The documentary follows the events of their lives from Ginsberg and Kerouac's meeting at Columbia University in 1944 to the deaths of Ginsberg and Burroughs in 1995. The film blends original footage of the trio from interviews with dramatic interpretations by modern actors to fully explore their characters. Additional performances by other beat artists, and modern-day interviews with those influenced by the Beat Movement round out the examination of how and why these men became icons of their generation.